1: aq. Na2CO3 / methanol / 4 h / 23 °C 2: ethyl acetate 3: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 4: 80 percent / 1N HCl / methanol / 2 h / Heating View Scheme

1: aq. Na2CO3 / methanol / 4 h / 23 °C 2: ethyl acetate 3: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 4: 80 percent / 1N HCl / methanol / 2 h / Heating 5: 80 percent / aq. K2CO3 / methanol / 12 h / 23 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />T=23&deg;C;&nbsp;P=2585.7&nbsp;Torr;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 95 percent / NaN₃, NH₄Cl / acetone; methanol / 20 h / Heating<br />2: 91 percent / DMAP / CH₂Cl₂ / 1 h / 23 &deg;C<br />3: 93 percent / H₂ / 10percent Pd-C / methanol / 4 h / 23 &deg;C / 2585.7 Torr<br /> <br /> &nbsp;